I started my new job in March 2018 as a 25 year-old paralegal, working towards my transfer exams that would take place a few months later. I treated myself to a re-work of the small tattoo I had on my upper back between my shoulderblades. I'd got it done in Berlin the previous year and I'd gone off it a bit, it seemed too small, and because of its location I hadn't been able to take care of it properly so it hadn't healed as well as it should have done. I didn't want a huge back piece but I could take it being a little bigger than it was, as well as being overall better quality. Plus I had Ryan to clean and dress it for me, bless him.
****
As I mentioned in the first chapter, now I was working full-time I dialled back my rent boy work a little bit. I saw clients a couple of nights at most during the work week, with more flexibility on weekends, but I was enjoying it too much to give it up and I started packing the money away. Some clients who'd liked my wildman lumbersexual look went off me when I went clean-cut, but that was a niche vibe anyway and it's not like I'd gone full-on metrosexual. My hair and beard were kept sharp, but my body hair was left to its own devices apart from my ballsack and shaft. Though I'd kept in good shape while backpacking, teaming up with Ryan in the gym and following his dietary habits helped me to return my physique to its best form and then exceed it.
****
My most regular client saw me every two-to-three weeks for nearly 18 months, which was a pretty impressive run. He was a youngish guy, not bad looking, but he had his thing and was willing to pay for it (given his regularity and the ease of the job, I ended up giving him a healthy loyalty discount!). He liked me to answer the door wearing nothing but briefs and either a baseball cap on backwards or a beanie (don't ask me what the hats were about, I guess he just liked the look). He'd firmly steer me where he wanted me, sometimes the kitchen, or the living room, or even no further than the hall by the front door, as long as we were where the floor was wipe-clean. We'd snog for a bit and he'd let me take his shirt off, then he'd drop to his knees, tug my briefs down and suck my cock. He'd have his bottoms (trousers, jeans, shorts, trackies, whatever he had on that day) pushed down at the front and his cock out so he could play with himself. Eventually I either filled his gob with spunk or spaffed over his chest, at which point he'd unload on the floor. I'd give him some kitchen towel to wipe the spillage up with, he'd sort his clothes out, hand me my cash and leave. Simple and so easy!
In fact, the majority of punters were uncomplicated. Naked on the bed, a bit of massage, a bit of making out, a bit of oral (either one-way or two-way). Maybe a little anal fingering if he was adventurous. Some clients wanted full anal - either giving or taking or both - but it was surprisingly uncommon.
****
I saw some punters who were inexperienced and wanted to pay an escort to help them through their first time. Of course they'd filled their heads with a lot of gay porn but usually their first few times followed a particular pattern. When I first met them, I'd spend time getting them to relax, being friendly and putting them at ease. We'd start with a naked massage and progress to us kissing and playing with each other's cocks. Sometimes they'd cum really quickly, sometimes it would take ages - nerves could result in either outcome. If they could last, I'd usually give them oral, but if they came quick, I'd guide them through sucking my cock; generally they'd get hard again fairly quickly so I could give them their money's worth.
If an inexperienced client came back for more, it was about working out whether to lead them down the top or bottom route next, though some guys had a definite hunger for what they wanted to try. If they wanted to fuck me it was fairly straightforward (and often quick), but if they wanted to experience getting fucked for the first time, there was more to it. I'd have to make gentle enquiries about whether they'd done a shit that day, for example, and if they'd showered since they had. I wasn't squeamish but I didn't want to fuck a gutfull of poo or lick a dirty asshole. To be honest, even virgins were usually clued up enough to know to take a dump and have a wash before coming over, and though some remained anxious about making a mess, I put them at ease. We'd move from massage and mutual oral to me rimming them and starting to open them up with a well-lubed finger or two, really slowly and gently, until they were ready to take it. Once they'd been fucked, there was no holding them back from then on. Some came back for more, some decided it wasn't for them, others no longer needed me and went out into the wild to hunt cock for themselves.
****
I'll be honest, my favourite clients were the older guys who were a bit dominant and wanted to take charge. With guys, I leaned towards bottoming as a matter of preference, I had just developed a real enjoyment of getting my asshole well fucked. Hotel clients were the best; visiting businessmen letting off steam away from their wives.
There was one guy I saw three or four times between mid-2018 and early 2019. Paul was an American businessman, in his late 40's, maybe 50, over six foot tall and with a burly build; he obviously worked out and lifted heavy but wasn't very diet conscious, so there was a bit of a gut along with the thick muscle of his torso and limbs. He was hairy, with his salt-and-pepper head hair in a short conservative style, and neatly-trimmed stubble on his face. He arranged our first meeting in the bar of his upmarket London hotel at 9.00 in the evening; I'd had time to go home to shower and clean up after work and was freshly suited and booted, as was he. He bought me a whisky and we chatted for half an hour before he led me to his room.
Once there, he paid me and I slipped the folded notes into my jacket pocket. Paul then took a small toiletries bag from his bedside cabinet and sat back in an armchair with the bag on the occasional table next to him. With an intensely sexy air of casual authority, he directed me to strip. I slowly removed my jacket, slipped off my tie and proceeded to open the top three buttons of my shirt. I then unlaced and removed my leather formal shoes and unbuckled my belt, sliding it out of the loops and putting it to one side with my jacket. Paul had me pause at that point and gestured me to come closer so he could run his hands up and down my trouser-covered thighs and over my ass. My hard cock started to leak in my tight CK boxer briefs as he told me to lie face down over his lap, then he started to squeeze my glutes and slap them hard, each stroke eliciting a gasp and a moan from me. He tugged the back of my shirt out from my trousers and ran his hand up my bare back, then pushed it under the waistband of my suit trousers and under my CK's, a finger sliding through my hairy crack, pausing before it reached my twitching cunt.
After a couple more firm slaps on the ass, he had me stand and remove my shirt and trousers, then turn and pose for him in my socks and underwear as he massaged the bulge in the front of his own pants. A curl of his finger and a commanding look, and I was removing his shoes for him, kissing and rubbing his socked feet, before getting back in position across his lap and getting my bum smacked some more. Fuck it was hot, and it only got hotter when he pushed the ass of my boxer briefs down and started to paddle my bare cheeks with his palm, pausing every so often to spread them and tease my tight hairy anus with a spit-wet fingerpad. "That's such a nice fuckin' hole boy," he'd murmer. His hand moved down into my undies to cup and tug my smooth balls, massaging and stretching them until they dangled out over the rear waistband of my boxers, then he added the occasional light tap to the bollocks as he continued to spank me. Eventually he pushed my undies down and over my socked feet so he could spread my legs wider and so my rock-hard and drooling cock was pressed against his suited thigh and pushed down towards the floor, ripe for occasional milking strokes in between spanking my butt and playing with my moist pussy hole. His focus on my cock increased after a while and I clutched his knee and drooled on it as I moaned at his firm strokes; the wanking paused when his spit-wet finger pushed into my asshole and expertly found my prostate and started to tap it.
After a time, when I started wondering if he wanted me to cum this way, he stopped. His thick legs shifted under my chest and abs as he leaned sideways to reach for the toiletries bag on the small table next to his chair. I heard it unzip, and he told me to spread my ass. I reached back and parted my glutes wide enough for my moist hole to wink open slightly, then there was a cool trickle of lube slipping down from the top of my crack. His fingers smeared the fluid over my ring, then I felt something bulbous pressing against it, some toy or another I guessed. It was cool, hard and smooth, not like rubber or plastic, more like steel or even glass; I tried to peer back over my shoulder but I couldn't see it. He ran the slippery smooth obeject teasingly over my sensitive hole, encouraging me to push my ass up and to make my hole flare open in little pulses. Finally he centred it on my pucker and started to apply steady firm pressure. The head of the toy was round and thick, not like the narrow tip of a traditional buttplug, and I had to relax to let it in. Though my hole was well-trained, I faked the expected whimpering sounds of half-pain, half-pleasure as my sphincter was forced open. As the toy slid up my chute, it got narrower and my hole could close more; if anything, it felt like a pestle, one of those granite kitchen tools you use to grind shit up with. Thanks to its wider head and narrower neck, it stayed put once it had slid all the way in, stopped from going further by another bulge towards the end. It made clinking sounds as he tapped the end of it with a ring on his finger, sending little shivery vibrations throigh my anus, then he eased it out slowly before pushing it back in again as I held my ass spread wide and he resumed milking my cock of its precum.
He left the toy in place when he finally slid me off his lap to the floor and had me shuffle around until I was resting on my upper back and shoulders, my hands bracing my lower back and my ass in the air, legs and socked feet over my head, my dripping cock pointing towards my mouth. He wriggled me back on the carpet until my back was wedged against the edge of the chair and he could lead forwards as he sat, his face over my ass. He spread me and started to play with the toy more vigorously, finally pulling it all the way out and punching it back in, and I could see it was indeed made of glass. I moaned with pleasure as my hole stayed progressively more open with each stroke, so he could dribble his spit right up my chute in between penetrations. As he played with my cunt he resumed jerking my cock, and he didn't stop even when I prostested; I opened my mouth wide and stuck out my tongue to receive the splashes of my own load over my face and beard as my awkwardly-postioned body shook with a powerful toe-curling orgasm. He milked the last drips out of me as he let the toy rest in my hole, then he helped me to my knees between his legs. Knowing what he wanted, I unzipped him and levered out his thick, hard, sticky, cut cock and sucked him to his hairy root, my cum dripping down my face and into his pubes, as I reached back behind me with one hand to stimulate my fucknut with that glass tool. As I swallowed and sucked him, my cock regaining full leaking hardness, he unbuttoned his shirt, and eventually stood up. He guided me into position, my knees on the arms of the chair, my arms and chest braced on its high back, as he sank to his knees and started to lap at my balls, taint and crack, his tongue flicking and teasing the edges of my stretched ring as he moved the toy in and out, pulling my hardon back between my legs so he could suck on the head. Standing again, he took a rubber from his toiletries bag and sheathed himself. His shirt spread open, trousers around his ankles, he eased the glass toy out of my ass and, as he replaced it with his cock, he reached around me and slid the wet butt-warm object into my mouth. I sucked my taste off it eagerly as he cupped my throat in his hands and squeezed lightly as his hard slamming fuck started up. He gave it to me hard for a good ten minutes, my own cock bouncing and leaking, before he pulled out and drew me off the chair so he could sit on it and I could turn my back to him and ride his tool. Finally, he pushed me to my knees on the carpet, stood and jerked his seed out to join mine on my face. Seeing I was still hard, he had me lie on the edge of the bed with my socked feet in the air and resumed punching my open cunt with the glass toy until I wanked out my second load.
He lay next to me for a while after that as we nursed spirits from the minibar and he let his hand roam over my body, until finally he gave me a towel to wipe down with and watched me get dressed. He gave me a generous tip just as I opened the door to leave.
****
The next time Paul called, I wasn't going to have time to go home and freshen up; he told me not to worry. I went straight up to his hotel room and he answered the door wearing nothing but a hotel bathrobe. Lying back on the bed, he had me strip slowly naked, then handed me a black plastic bag; peering inside, I saw a transparent plastic package containing a douche bulb - Paul had been shopping! I took it to the bathroom and cleaned out my ass with warm water before having a quick shower (Paul told me to leave the bathroom door open and he watched me the whole time), drying off and padding naked back into the main room.
"Show me your ass", he growled, and I stood at the foot of the bed, turned around, bent at the waist and spread my cheeks. I heard him slide down the bed, his bare feet settling on the carpet between mine, and felt his breath on my exposed manhole. "Push it out for me", he ordered, and I bore down with my abs to make the sphincter flare open and puff outwards. Just as it did, his broad wet tongue swept over the sensitive anal flesh and I let lose a loud involuntary moan. He chuckled and started to work his tongue over my asshole, lapping at it like a dog at a bowl, before starting to firm his tongue up and force it through the ring to taste my chute. "Such a nice hole Dave," he murmured between tongue-fucks.
"Do you fuck girls?" he asked. An odd question. "Yeah, I fuck girls," I answered. "Then get on the bed and show me how you do it", he ordered. Slightly confused, I lay on my front crossways on the bed, pushed my upper body off the mattress with my arms, and started to hump the bedclothes in slow, sensual moves. "Like this?" I asked. "Yeah, like that, show me how they like it." I kept it up, moving my hips in circles. "Move your legs wider apart" he commanded, and I did as I was told. "Fuck, I'd like to do a girl with you boy, do you know any working chicks?" Unfortunately I didn't. He grunted, got in front of me and slid his bathrobe off as he pushed his cock down my throat, fucking it as I fucked the bed. After a few minutes, he pushed my upper body down and got on the bed, his knees on either side of my head, lay down across my body so his face was at my ass, and spread my glutes wide before resuming his hungry rimjob. I held onto his thighs and moaned as he held my hole open and drooled his spit into it, then ground his stubble into my ass and ate me out. I could feel his hot pulsing hardon on the back of my head, leaking onto my neck. He reached under me and pulled my hardon down so it was uncomfortably pointing towards my feet and wanked it as he licked my anus, before grabbing my ankles, pulling my bare feet toward him, sucking on my toes and nuzzling the soles for a bit. I squirmed and giggled, and that just made him laugh and redouble his tickling. Eventually he got off me, flipped me onto my back, dragged me back a bit until my head was off the edge, and resumed fucking my throat while he molested my sweating bod.
When he was ready to fuck me, he did it doggie-style for a while, his thick sheathed meat sliding in and out of my well-lubed shitchute and making me fuckin' grunt with pleasure as he delivered the occasional firm slap to my quivering hairy glutes. Rolling me onto my back to do some missionary, he snogged me hard and had me tell him how hot he was, how I loved his man's cock in my fag pussy (that kind of dirty talk isn't my favourite, but hey, he was paying), then he had me open my gob so he could repeatedly spit in it. He had great staying power but he got tired after a wile, so I straddled him and rode that dick hard while he wanked me with a lubed hand. He urged me on - "Fuckin' cum for me boy, show me how much you like Daddy's dick up your ass" - until I spat ropes of jizz across his chest. He scooped up some of my seed and fed it to me on his fingers until he filled the condom with his gravy.
****
Later in 2018, Ryan had persuaded me that my muscle definition would really rock if I shaved all over like he did. So I reluctantly shaved my chest, belly, shoulders and ass, and trimmed my armpits, pubes, arms and legs down pretty short (Ryan did the honours on my lightly-hairy back for me). I combined it with a mid-fade haircut but with the hair on top long enough to slick back, plus trimming my beard right down to designer stubble. Ryan was right, I looked like a fitness model, and I got super serious for a while about diet and so on. I was to keep that look for over a year (requiring some fresh profile shots so as not to get accused of false advertising), and when I visited Sydney for Christmas/New Year in 2018/19, I have to admit it felt good to have so much skin exposed to the sun, and my tan rocked as a result. I wasn't a fan of the slick sweatiness between my smooth asscheeks but I guess everything has a downside. After a few months of shaving, I even tried getting waxed - actually, sugared, at a place called "The Sugar Shop" on Commercial Street (sadly now closed). Chest, abs, back, sack and crack, with everything else trimmed - they did a great job, and I found it quite erotic. They never gave me a happy ending - it wasn't that sort of place - but they were completely relaxed about my hard leaking cock, said it was normal, and that it made it easier to sugar the shaft anyway.
****
The next and last time I saw Paul was in early 2019 (by which time I was 26). He'd found a female escort and put us in touch, and we worked out a deal for a three-way session. We met for drinks at his hotel bar and then retired to his room where we continued drinking and progressively stripping off, taking turns snogging the girl and each other. I think Paul was surprised - and maybe just a bit disappointed - when he saw my nearly hairless body, but he didn't say anything (and the girl seemed to really like it). We proceeded to fuck for nearly three hours, Paul and I taking turns on her or doing her together. He really seemed to like watching me fuck her and took the liberty to feel my body up and play with my smooth balls and ass as I drove into her cunt. He had me shoot my first load on her face and tits, but saved his own cum for my face, which she then licked off me. He managed another load and I managed two more that night.
The chick and I made good money from that session, but I never saw Paul again after that. I did suspect he wasn't keen on my new look but I wasn't worried; having been a consistently hairy bastard for most of my adult life I was enjoying the novelty of being manscaped and smooth, and I kept it up until early 2020.
****
I'd started seeing one particular client - lets call him "Jayden" - in mid-2019. He was a cute young guy, barely 20 years old, mixed race, small-built and lean-bodied, his hairless coffee-coloured skin scattered with little sketchy tatts; He had a nice thick dick swinging between his legs too. He wasn't yet sure if he was gay, bi, bi-curious, hetero-flexible, pan or whatever, so he was still firmly in the closet while he worked things out in his head. I'd seen him a couple of times, first letting him fuck me with that fat meat, then on the second occasion I'd introduced him to getting topped, which he'd loved. He was quite the pocket-rocket.
On one rare evening when we had no other plans, Ryan and I were chillin' at home and settling in to watch a movie. I was wearing soft cotton gym shorts, commando and bare-chested 'cos it was a warm evening, while Ryan had on a pair of boxer briefs with nothing over the top of them, and an oversized stringer vest that was basically pointless because his broad, smooth pecs and their little nips were fully exposed. My phone buzzed with a WhatsApp and it was Jayden: "U free now?" I showed it to Ryan and he shrugged and said "I can find something to do for an hour if you want". When I told Jayden I was free, he replied with "U no any1 4 a 3sum? Want to try". I did know a couple of guys as it happened, but it would have been an ass-ache to find out if they were available, waiting for them to respond, and then to get over to the flat. So I showed the message to Ryan and said "What do ya reckon, you up for it?" He'd brought me in on his City trader client again since the first time we'd done it, but he looked unsure and asked what Jayden was like; once I described him, he said "Yeah OK but I'm top only, yeah?" I replied to Jayden in the affirmative (saying "mate is top only, cool?") and agreed a price that I'd split with Ryan 50/50. He was half an hour away so I went to get out the condoms, lube and kitchen towel and put them on the coffee table.
Jayden rocked up wearing super-baggy cargo shorts, a tight vest and those chunky trainers that make your feet look huge; he knew the rules and toed them off inside the door, following me into the flat barefoot. Ryan stood as I introduced him, and they awkwardly man-hugged a greeting. I left them to get acquainted while I took Jayden's money into the kitchen and hid it under the cutlery tray in the top drawer, and when I came back they were still standing there making small talk. I slipped my arm around Jayden's slight shoulders and drew him in for a deep kiss as Ryan watched. He and I then settled down on the sofa as Jayden got to his knees in front of us, drew my semi out of the leg of my shorts and started to suck me to full hardness as I reached across to massage the bulge in Ryan's boxer briefs. As Jayden worked me down his throat, he slipped my shorts down and over my bare feet so I was fully naked, and I felt Ryan's eyes on me - I'd always known that one reason Ryan had wanted me to lose my body hair was that he was turned on by smooth bodies, and I was more than cool with that. At this time my pubes were clippered so short they were barely there, and it made my cock look much bigger than usual. Ryan got up and stood next to Jayden, so he moved from my cock to Ryan's, pulling his tight boxers down to unleash his full-hard cock and working it down his throat as I started wanking mine. Ryan caught my eyes and I took his hand and guided a couple of his fingers to my mouth and sucked them, so he began to feel around the inside of my mouth, fascinated.
I stood and peeled Ryan's pointless vest off him so he was naked while Jayden swapped his mouth from cock to cock, trying to give us both equal attention. I then got on my knees next to Jayden and took turns with him sucking Ryan's cock. Then, as he continued to blow Ryan, I got behind the lad and tugged his loose shorts and underwear down to expose his ass. I gave his skinny shanks a slap or two then spread his buns and started to lick his smooth, tight asshole as Ryan watched. Moaning, Jayden paused his sucking so Ryan could peel off his vest, then got back to it as I continued to lap at his boyhole, pausing once or twice to spit on it. I didn't want him open, I wanted him to feel it, so I rubbered up, lubed my dick and smeared the excess up his crack. Placing my cockhead at his wet pucker, I dribbled some spit down on it then slowly forced my cock through his tight ring until I was balls-deep up in his rectum, savouring the squeal Jayden made around a mouthful of Ryan's cock. I rested for a few seconds so he could get used to it a bit, before gripping his hips and starting to fuck. After a while, Ryan wanted a go, so we swapped ends - I crouched down and sucked Ryan's cock for a minute before rubbering him up and spitting on Jayden's cunt for him and guiding him in, then I got up and made Jayden suck his own assjuices off my sheathed knob as Ryan punched up into his guts. Jayden rose up on his haunches to snog me as Ryan ground his gear up his ass, and after a few minutes he whispered to me "Can I have a go on you?" I smiled and nodded and motioned to Ryan to slow down and withdraw.
I knelt on the sofa as Jayden crouched behind me and started to eat out my smooth waxed ass, and I got Ryan to strip off his condom, get up next to me and feed his fat leaking tool into my gob. Soon I felt Jayden's thick dong pushing through my ass and up into my rectum, and the excited little puppy just started hammering away at my guts as I gasped and let out a shocked little laugh. After a while, Ryan rolled on a fresh condom, gently nudged Jayden out of the way and flipped me over onto my back; I looked up into his face with surprised anticipation, as he'd never fucked me before, and he grinned at me as he held back one of my legs by the ankle (as Jayden pulled back my other one and started to suck my toes while he wanked) and used his free hand to guide his dick into my wet hole. He started fucking me hard, and I wished more than anything that I could pull his face to mine and kiss him, but something told me that wasn't on the table. He and Jayden took turns on my ass for a while before Ryan slumped down next to me on the sofa, his arm around my shoulders, and Jayden rode our dicks, one after the other, back and forth.
I wanted to do Jayden doggie some more, so we got into position (him kneeling on the sofa, me standing behind him) and I started to slam him, slowing down only when Ryan nuzzled up behind me and pushed two fingers up my ass, frigged my prostate for a bit as I fucked, and then stuffed his dick back up into my rectum so I was the middle of a fuck sandwich. I eventually pulled out of Jayden's hole and started to eat that sloppy pussy while Ryan continued to fuck me, then he and I tag-teamed Jayden's ass. We tried double-penetrating Jayden but we didn't get far enough into it before he called time, which is fair enough, and when I took a turn sitting on Jayden's dick, Ryan couldn't get the hang of stuffing his cock in along side it - understandable, it takes skills! We reverted to spitroasting Jayden for a while, swapping ends frequently so the lad got plenty of ass-flavoured latex in his mouth, then had him lie down on the sofa as we discarded our dirty rubbers. I started to jerk off but Ryan put his hand on the back of my neck and pulled me down to suck him for a bit, then I just had to get back upright so I could wank my load out over Jayden's face and tongue. As Ryan got in close to do the same, I got my face down and gob open right close to Jayden's so he could spaff his scum over both of us. I snogged Jayden's cummy lips and sucked the last drips out of Ryan's cock. Finally, I shoved three fingers up Jayden's cunt and banged him as I deepthroated his fat tool, until he took control and jerked his own boyjuice out - he hit his own chin and liberally basted his chest.
Ryan sat back and watched as I massaged the three loads into Jayden's skin, 'cos he liked to wear it going home, and gave him a passionate kiss as I sent him out the door. I high-fived a grinning, sweaty Ryan as I headed past him to the shower - to my surprise, a minute later he stepped in with me. We didn't kiss, but we did tenderly wash each other, and afterwards I slipped my shorts back on as Ryan donned his boxer briefs (but left his vest off). We settled down to watch the move with a couple of beers, and Ryan got me to lie on the sofa with my head in his lap and his arm draped across my chest. I confess, I felt really warm and fuzzy inside, and though I knew it would never go anywhere beyond fuck buddies, I had to admit to myself that I was a little bit in love with the lad.
As promised, this is a true account of my experiences as I remember them. I'd love to hear what you think of it, so email me if you want at [email protected]
